(6Z,8E)-11-hydroxy-6,8-henicosadiene | 188954-67-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (6Z,8E)-11-hydroxy-6,8-henicosadiene
• 英文别名: (Z)6,(E)8-Heneicosadien-11-ol；6Z,8E-heneicosadien-11-ol；(6Z,8E)-henicosa-6,8-dien-11-ol
• CAS: 188954-67-8
• 化学式: C₂₁H₄₀O
• 分子量: 308.548
• InChiKey: BJBRRXFULITXAA-WREYUNAZSA-N

物化性质

• 沸点：
  415.6±14.0 °C(Predicted)
• 密度：
  0.856±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  22
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6Z,8E)-11-hydroxy-6,8-henicosadiene 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以79%的产率得到(Z)-6,(E)-8-heneicosadien-11-one
  参考文献：
  名称：

  彩绘苹果蛾Teia anartoides雌性信息素的四个成分的合成。

  摘要：

  合成了澳大利亚害虫苹果雌蛾（Teia anartoides）的四个信息素成分。这些是（Z）-6-henicosen-11-one（1），（6Z，8E）-6,8-henicosadien-11-one（2），（Z）-cis-9,10-epoxy-6-亚油（3）和（Z）-顺-9,10-环氧-6-二十烷（4）。将2-十二烷酮转化为1和2，并且由4-叔丁基二甲基甲硅烷氧基-顺式2，3-环氧-1-丁醇的对映体合成3和4的对映体。

  DOI：

  10.1271/bbb.67.1559
• 作为产物：
  描述：

  十一醛 在 吡啶 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 水 为溶剂， 反应 14.0h， 生成 (6Z,8E)-11-hydroxy-6,8-henicosadiene
  参考文献：
  名称：

  (Z)6, (E)8-Heneicosadien-11-One: Synergistic Sex Pheromone Component of Douglas-Fir Tussock Moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae)

  摘要：

  Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and (Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified in pheromone gland extracts of female Douglas-fir tussock moths (DFTM), Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram quantities in extracts and structural conversion during analytical procedures and bioassays complicated chemical identifications. Complete identification required comparative analyses of stereoselectively synthesized and female-produced dienones by coupled gas chromatographic-electroantennographic detection (GC-EAD), high-performance liquid chromatography (HPLC) and coupled GC-mass spectrometry (MS). Determination of the pheromone component was contingent upon an experimental design that minimized structural rearrangement of dienones before and during the field test. In a 40-min field experiment, acetonitrile solutions of each of the above dienones were carried on Dry Ice to traps and were syringed onto cotton release devices below trap lids. In combination with the previously known sex pheromone component of DFTM, (Z)6-heneicosen-11-one (Z6), Z6E8 was the only synergistic dienone and the mixture was highly attractive. Because Z6 by itself attracts seven species of tussock moths (two sympatric with DFTM), a blend of Z6 and Z6E8 may impart specificity to DFTM pheromone communication. In commercial lures, this binary blend may facilitate species-specific, sensitive monitoring and efficacious control by mating disruption of this important forest defoliator.

  DOI：

  10.1023/b:joec.0000006343.38471.c7

文献信息

• Synthesis of the Four Components of the Female Sex Pheromone of the Painted Apple Moth,<i>Teia anartoides</i>
  作者：Shin-etsu MUTO、Kenji MORI

  DOI：10.1271/bbb.67.1559

  日期：2003.1

  Four pheromone components of the female painted apple moth (Teia anartoides), an Australian insect pest, were synthesized. These were (Z)-6-henicosen-11-one (1), (6Z, 8E)-6,8-henicosadien-11-one (2), (Z)-cis-9,10-epoxy-6-henicosene (3), and (Z)-cis-9,10-epoxy-6-icosene (4). 2-Dodecanone was converted to 1 and 2, and both the enantiomers of 3 and 4 were synthesized from the enantiomers of 4-tert-bu

  合成了澳大利亚害虫苹果雌蛾（Teia anartoides）的四个信息素成分。这些是（Z）-6-henicosen-11-one（1），（6Z，8E）-6,8-henicosadien-11-one（2），（Z）-cis-9,10-epoxy-6-亚油（3）和（Z）-顺-9,10-环氧-6-二十烷（4）。将2-十二烷酮转化为1和2，并且由4-叔丁基二甲基甲硅烷氧基-顺式2，3-环氧-1-丁醇的对映体合成3和4的对映体。
• Synthesis of 6Z,8E-heneicosadien-11-one, a sex pheromone of the painted apple moth, Teia anartoides
  作者：Jasmine C. Jury、Simon Fielder、Markandu Vigneswaran

  DOI：10.1016/s0040-4039(02)02515-7

  日期：2003.1

  6Z,8E-Heneicosadien-11-one, a sex pheromone of the painted apple moth, Teia anartoides has been prepared in seven steps from 1,2-epoxydodecane in an overall yield of 25%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Stereospecific synthesis of all four isomeric 6,8-heneicosadien-11-ones: sex pheromone components of the painted apple moth Teia anartoides
  作者：Daniel J. Comeskey、Barry J. Bunn、Simon Fielder

  DOI：10.1016/j.tetlet.2004.08.095

  日期：2004.10

  The stereospecific synthesis of all four isomeric 6,8-heneicosadien-11-ones, sex pheromone components of the painted apple moth, Teia anartoides, is reported using the Suzuki-coupling of vinyl boronic acid and vinyl iodide intermediates.

  据报道，使用乙烯基硼酸和乙烯基碘化物中间体的Suzuki偶联，所有四个异构体6,8-heneicosadien-11-ones，涂苹果蛾Teia anartoides的性信息素成分都进行了立体定向合成。
• (Z)6, (E)8-Heneicosadien-11-One: Synergistic Sex Pheromone Component of Douglas-Fir Tussock Moth, Orgyia pseudotsugata (McDunnough) (Lepidoptera: Lymantriidae)
  作者：Gerhard Gries、Keith N. Slessor、Regine Gries、Grigori Khaskin、Priyantha D. C. Wimalaratne、Tom G. Gray、Gary G. Grant、Alan S. Tracey、Mike Hulme

  DOI：10.1023/b:joec.0000006343.38471.c7

  日期：1997.1

  Three candidate sex pheromone components, (Z)6,(Z)9-, (Z)6,(E)8-, and (Z)6,(E)9-heneicosadien-11-one (Z6Z9, Z6E8, and Z6E9) were identified in pheromone gland extracts of female Douglas-fir tussock moths (DFTM), Orgyia pseudotsugata (McDunnough). Their occurrence in subnanogram quantities in extracts and structural conversion during analytical procedures and bioassays complicated chemical identifications. Complete identification required comparative analyses of stereoselectively synthesized and female-produced dienones by coupled gas chromatographic-electroantennographic detection (GC-EAD), high-performance liquid chromatography (HPLC) and coupled GC-mass spectrometry (MS). Determination of the pheromone component was contingent upon an experimental design that minimized structural rearrangement of dienones before and during the field test. In a 40-min field experiment, acetonitrile solutions of each of the above dienones were carried on Dry Ice to traps and were syringed onto cotton release devices below trap lids. In combination with the previously known sex pheromone component of DFTM, (Z)6-heneicosen-11-one (Z6), Z6E8 was the only synergistic dienone and the mixture was highly attractive. Because Z6 by itself attracts seven species of tussock moths (two sympatric with DFTM), a blend of Z6 and Z6E8 may impart specificity to DFTM pheromone communication. In commercial lures, this binary blend may facilitate species-specific, sensitive monitoring and efficacious control by mating disruption of this important forest defoliator.